Asymmetric 2,4-Dienylation/[4 + 2] Annulation Cascade to Construct Fused Frameworks via Auto-Tandem Palladium Catalysis
Jian‐Xiang Zhu, Fu Pi, Teng Sun, Wen-Yu Huang, Lu Gao, Zhichao Chen, Wei Du, Ying‐Chun Chen
Abstract
-functionalized aryl enones and 2,4-dienyl carbonates has been presented, proceeding through sequential 2,4-dienylation/Michael addition/π-σ-π isomerization/allylic alkylation. A broad array of enantioenriched architectures having fused and spirocyclic frameworks are constructed in moderate to excellent yields and stereoselectivity. Notably, the intrinsic intramolecular Diels-Alder reaction pattern of the dienylated intermediates is well reversed via Pd(0)-π-Lewis base catalysis.
Topics & Concepts
ChemistryAnnulationTandemIsomerizationTsuji–Trost reactionCascade reactionIntramolecular forceCatalysisPalladiumStereoselectivityArylCombinatorial chemistryLewis acids and basesAllylic rearrangementStereochemistryOrganic chemistryComposite materialAlkylMaterials scienceCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesAsymmetric Synthesis and Catalysis